1-[(Z)-4-methoxybut-3-en-1-ynyl]naphthalene | 154116-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(Z)-4-methoxybut-3-en-1-ynyl]naphthalene
• CAS: 154116-16-2
• 化学式: C₁₅H₁₂O
• 分子量: 208.26
• InChiKey: QFJWISRDYLMMGV-XGICHPGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[(Z)-4-methoxybut-3-en-1-ynyl]naphthalene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 1-[(E)-4-(Methoxy-dimethyl-silanyl)-4-trimethylsilanyl-but-3-en-1-ynyl]-naphthalene
  参考文献：
  名称：

  Photochemistry of 1-Aryl-4-(pentamethyldisilanyl)-1,3-butadiynes

  摘要：

  All the 1-aryl-4-(pentamethyldisilanyl)-1,3-butadiynes (1a-d) synthesized show strong phosphorescence emissions with triplet energies around 218-260 kJ/mol. Laser photolysis of 1-(p-nitrophenyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1d) in polar solvents results in the formation of an interesting transient (zwitterion species) through intramolecular electron transfer from disilanyl to the nitro group in the triplet excited state. Irradiation of 1d in methanol or ethanol gives 1-(p-nitrophenyl)-1,3-butadiyne (8) through C-Si bond cleavage from the transient. Photolysis of 1-phenyl-4-(pentamethyldisilanyl)-1,3-butadiyne (1a), 1-(1-naphthyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1b), and 1-(p-methoxyphenyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1c) in methanol yields photoaddition products (2-7) through silacyclopropene intermediates.

  DOI：

  10.1021/jo00084a031
• 作为产物：
  描述：

  (Z)-1-methoxybut-1-en-3-yne 、 1-碘萘 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 作用下， 以 三乙胺 为溶剂， 反应 0.83h， 以78%的产率得到1-[(Z)-4-methoxybut-3-en-1-ynyl]naphthalene
  参考文献：
  名称：

  Photochemistry of 1-Aryl-4-(pentamethyldisilanyl)-1,3-butadiynes

  摘要：

  All the 1-aryl-4-(pentamethyldisilanyl)-1,3-butadiynes (1a-d) synthesized show strong phosphorescence emissions with triplet energies around 218-260 kJ/mol. Laser photolysis of 1-(p-nitrophenyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1d) in polar solvents results in the formation of an interesting transient (zwitterion species) through intramolecular electron transfer from disilanyl to the nitro group in the triplet excited state. Irradiation of 1d in methanol or ethanol gives 1-(p-nitrophenyl)-1,3-butadiyne (8) through C-Si bond cleavage from the transient. Photolysis of 1-phenyl-4-(pentamethyldisilanyl)-1,3-butadiyne (1a), 1-(1-naphthyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1b), and 1-(p-methoxyphenyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1c) in methanol yields photoaddition products (2-7) through silacyclopropene intermediates.

  DOI：

  10.1021/jo00084a031

文献信息

• Photochemistry of 1-Aryl-4-(pentamethyldisilanyl)-1,3-butadiynes
  作者：Jang Hyuk Kwon、Seong Taek Lee、Sang Chul Shim、Mikio Hoshino

  DOI：10.1021/jo00084a031

  日期：1994.3

  All the 1-aryl-4-(pentamethyldisilanyl)-1,3-butadiynes (1a-d) synthesized show strong phosphorescence emissions with triplet energies around 218-260 kJ/mol. Laser photolysis of 1-(p-nitrophenyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1d) in polar solvents results in the formation of an interesting transient (zwitterion species) through intramolecular electron transfer from disilanyl to the nitro group in the triplet excited state. Irradiation of 1d in methanol or ethanol gives 1-(p-nitrophenyl)-1,3-butadiyne (8) through C-Si bond cleavage from the transient. Photolysis of 1-phenyl-4-(pentamethyldisilanyl)-1,3-butadiyne (1a), 1-(1-naphthyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1b), and 1-(p-methoxyphenyl)-4-(pentamethyldisilanyl)-1,3-butadiyne (1c) in methanol yields photoaddition products (2-7) through silacyclopropene intermediates.